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11161 Roland Parks Rd, Chance
$249,900
3 Beds ⋅ 4 Baths
Welcome to your island escape in Chance, Maryland—a serene coastal retreat for true nature lovers, just steps from the Tangier Sound and a short boat ride to the Chesapeake Bay. This beautifully updated three-bedroom, three-bath home offers a sought-after first-floor primary suite, with two generously sized upstairs bedrooms featuring ample closet space. Designed for indoor-outdoor living, the home features three private screened-in porches—perfect for enjoying morning coffee, evening breezes, and peaceful sunsets year-round. Two oversized sheds (12x24 and 12x20) provide exceptional space for storage, hobbies, or a workshop. Inside, you’ll appreciate fresh paint throughout and brand-new heating and cooling systems, making this home truly move-in ready. Whether you’re searching for a weekend getaway or a full-time coastal residence, this property offers comfort, functionality, and charm. As an added bonus, the community features private beach access and boat access, offering effortless entry to some of the Bay’s best boating, fishing, and outdoor adventures—right from your own neighborhood. Don’t miss this rare opportunity to own a peaceful waterfront retreat in a truly special setting. And for a bit of fun—keep an eye out for a hidden Mickey during your tour!

11161 Roland Parks Rd, Chance

Listing courtesy of The Parker Group. Contact:

27947 Fairmount Rd, Westover
$1,250,000
4 Beds ⋅ 3 Baths
Cedar Point Farm is a rare, intact nineteenth-century Chesapeake farmstead set along the Big Annemessex River between Manokin and Upper Fairmount. Approached by a long, tree-lined lane from Fairmount Road, the property encompasses upland fields, mature woodland, tidal marsh, ponds, and more than 2,200 feet of protected river frontage. The landscape is one of the most historically significant and ecologically rich tracts remaining in lower Somerset County. Originally constructed in the third quarter of the nineteenth century, the farmhouse reflects the architectural transition of rural Somerset during this period. Tradition and documentary evidence associate its principal construction phase with the 1881 marriage of Mary “Mollie” E. Ballard and Charles A. Curtis, descendants of the long-established Waters and Ballard families of Tudor Hall. The two-story side-hall/parlor plan features original arched doorway trim, turned newel post, walnut stair rail, rear service wing, and a two-story porch with lattice balusterwork. Subsequent early-twentieth-century improvements added a west wing and shed dormers while retaining the overall historic character. Accompanying the residence are several nineteenth- and early-twentieth-century outbuildings, including a board-and-batten barn, beaded weatherboard smokehouse, pump houses, sheds, and remnants of an earlier detached kitchen chimney. These structures reinforce the authenticity and continuity of the farm as a working Chesapeake landscape. Cedar Point Farm consists of two contiguous parcels—Tax Map 39, Parcels 363 and 193—held together as a single historic property. Both parcels are protected in perpetuity under a 2016 Conservation Easement granted to the Maryland Environmental Trust (MET) and the Lower Shore Land Trust (LSLT). The easement was established to preserve the property's agricultural productivity, forest resources, wetlands, wildlife habitat, and scenic Chesapeake shoreline. The easement safeguards approximately: 111 acres of mature forest, 36 acres of tidal and forested wetlands, 2 acres of ponds, 2,280 linear feet of Big Annemessex River frontage, and Habitat for Forest Interior Dwelling Birds and State-significant species. The land lies within a Targeted Ecological Area designated by Maryland DNR and sits adjacent to the Fairmount Wildlife Management Area and Chesapeake Forest Lands, forming part of a more than 5,000-acre protected block of conserved Chesapeake habitat. A mandatory 100-foot natural buffer along the river restricts disturbance and maintains the property’s scenic and ecological integrity. Property is subject to a no hunting covenant held by the current owner. GIS acres and deeded acres do not align. Buyer to perform their own due diligence. Additional information and documents available through listing agent.

27947 Fairmount Rd, Westover

Listing courtesy of The Land Group. Contact:

232 N Somerset Ave, Crisfield
$199,000
3 Beds ⋅ 3 Baths
RENOVATED VICTORIAN IN THE CRAB CAPITAL OF THE UNITED STATES! Welcome to the waterfront town of Crisfield, home of the annual Hard Crab Derby, the Soft Crab Celebration and the J. Millard Tawes Crab and Clam Bake. This small town hosts these large events as well as the Wheels on the Waterfront Classic Car Show and the Bluegrass Festival. Crisfield is home to the Somers Cove Marina, whose natural harbor hosts yachts, sailboats and ferry boats. Other waterfront harbors host recreation boats as well as working seafood boats. Located on high ground is this 3 Bedroom, 3 Full Bathroom Victorian that is nestled on a .521 acre fully fenced in lot. The updates include a full house HVAC system comprising of Ductless Min-Splits, thermal pane tilt-in Windows, the addition of two New Bathrooms, new Stainless Steel Kitchen Appliances, new Hot Water Heater, and new Washer and Dryer on the inside. On the outside there is fencing encapsulating the entire property, a new shed and a detached garage. The electrical and plumbing system have also been upgraded. The house offers Hardwood, LVP and Terra Cotta Floors, The home is located five minutes from local restaurants and specialty shops, ten minutes from Janes Island State Park that offers walking trails and waterfront sports and the Great Hope Golf Course. Crisfield was voted as One of the Safest Cities in America and it's the home of the Ward Brothers, nationally recognized wildlife artists and decoy carvers. The downtown boardwalk pavilion offers gorgeous sunsets and twilight view of Smith Island. If you are looking for a town that honors it's historic waterfront heritage but possesses modern conveniences, Crisfield checks all of your boxes. Contact the listing agent to make a showing appointment. Seller is listing this property at a reduced price and is selling it "As Is. Where Is".

232 N Somerset Ave, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact:

5111 Old Auger Rd, Crisfield
$450,000
3 Beds ⋅ 3 Baths
Discover the perfect blend of coastal charm and modern luxury in this stunning 3-bedroom, 3-bathroom home nestled in the desirable Annemessex Ridge community. With some renovations done 2025, this property promises to elevate your living experience to new heights. Step inside to find an inviting interior that boasts a traditional floor plan, ideal for both entertaining and everyday living. The gourmet kitchen is a chef's dream, featuring ample counter space and a cozy breakfast area that invites casual dining. The family room, conveniently located off the kitchen, is perfect for gatherings, while the elegant dining area sets the stage for memorable dinner parties. Retreat to the primary bedroom, where you will canal views create a serene escape. Outside, the property shines with extensive hardscaping and beautifully landscaped grounds, offering a picturesque setting for relaxation and outdoor activities. Enjoy the tranquility of your private canal-front lot, complete with 90 feet of waterfrontage and a private dock site, perfect for boating enthusiasts. Community boat launch ramp, your aquatic adventures await just steps from your door. The expansive 0.47-acre lot features bulkheaded and rip-rapped areas, ensuring both beauty and functionality. Spend your evenings on the porch or patio, soaking in the stunning water views and the gentle sounds of nature. Located in a peaceful canal setting, this home offers the perfect balance of privacy and accessibility. Enjoy the convenience of nearby amenities while relishing the tranquility of waterfront living. With an attached carport and ample driveway space, parking is a breeze. This exceptional property is not just a home; it's a lifestyle. Embrace the coastal living experience and make this dream home your reality. Don't miss the opportunity to own a piece of paradise in Annemessex Ridge! Possible owner is owner financing.

5111 Old Auger Rd, Crisfield

Listing courtesy of LAIRD & ASSOCIATES. Contact:

26934 Old State Rd, Crisfield
$135,000
1 Beds ⋅ 1 Baths
Discover a unique investment opportunity with this charming 3-bedroom, 1-bathroom farmhouse-style property, built in 1900 and situated on a generous 1.42-acre lot. This detached home, while requiring major rehabilitation, presents a blank canvas for savvy investors looking to capitalize on the potential for significant returns in a growing market. The property boasts a spacious 1,650 square feet of finished space, offering ample room for creative renovations. With its classic farmhouse architecture, there is potential to restore its historic charm while modernizing the interior to meet contemporary standards. Investors can explore various strategies, from a full renovation to a complete rebuild, depending on their vision and investment goals. The expansive lot provides opportunities for outdoor enhancements, such as landscaping, gardening, or even the addition of rental units, subject to local zoning regulations. The absence of an HOA means fewer restrictions and more freedom to develop the property as desired, maximizing your investment potential. Located in an area with increasing demand for housing, this property is poised for appreciation. The combination of its size, location, and potential for renovation makes it an attractive option for both short-term flips and long-term rental strategies. Investors can take advantage of the growing trend of buyers seeking unique, character-filled homes in desirable locations. Parking is convenient with a driveway, and the property is easily accessible, making it appealing for future tenants or buyers. This property is not just a home; it's a strategic investment opportunity waiting for the right vision. With the right renovations, this farmhouse can transform into a sought-after residence, yielding substantial returns in a competitive market. Don't miss your chance to invest in a property with endless possibilities!

26934 Old State Rd, Crisfield

Listing courtesy of LAIRD & ASSOCIATES. Contact:

29769 Kingston Ln, Westover
$300,000
4 Beds ⋅ 3 Baths
Discover incredible space and potential at 29759 Kingston Lane in Westover, Maryland — a 4-bedroom, 3 bath home with over 2,600 square feet of living area, set on nearly two acres of peaceful countryside. Offering exceptional square footage and versatility for the price, this home is ready for its next chapter with room to update and make it your own. Inside, the spacious floor plan features a large living room, formal dining area w/ gas firepalce, and a bright eat-in kitchen with plenty of cabinet space. A first-floor bedroom provides convenience and flexibility, while upstairs you’ll find a primary ensuite, additional bedrooms, a full bath, loft area, generous closet storage, and a bonus room perfect for a home office, playroom, or hobby space. Enjoy the outdoors on the screened porch or entertain on the large rear deck overlooking a private, wooded backdrop. The property includes a two-car garage and multiple outbuildings, all with electric — including a finished building ideal for an art studio, craft area, fitness room, or home-based business, plus a large lean-to storage shed and an additional powered storage space for tools or equipment. The home also features solar panels for energy savings, a roof replaced about five years ago, tankless hot water system, and a wooded setting that enhances the sense of privacy and country charm — all just a short drive from Crisfield’s shops, restaurants, and waterfront attractions. With its generous size, flexible layout, and versatile outdoor spaces, this property offers remarkable value for the money — a wonderful opportunity to enjoy space, privacy, and potential in a tranquil Eastern Shore setting.

29769 Kingston Ln, Westover

Listing courtesy of Real Broker, LLC - Salisbury. Contact:

225 N N Somerset Ave, Crisfield
$199,000
3 Beds ⋅ 2 Baths
Welcome to Crisfield, the Crab Capital of the United States! Located close to Crisfield High School is this INVESTOR ALERT! This charming home has a one year lease for $1,700 per month. As soon as you purchase the home you collect the rent. The home has been renovated and it offers 3 Bedrooms and 2 Bathrooms. The 20'x8' Three Season Front Porch has jalousie windows and wooden floors. The first floor offers an 18'x14' Living Room with a Gas Fireplace, a 16'x14' Dining Room, a 13'x11' Kitchen with an Electric Stove and a Stainless-Steel Refrigerator. There's a 13'x8' Sunroom and a rear 8'x9' private Rear Porch. Rounding out the first floor is a Utility Room and a Full Bathroom with a Step-In Shower. The second floor has 3 Bedrooms, all with Walk-In Closets and a Full Bathroom with a Step-In Shower. There is a lower-level 26'x20' Enclosed Room that is used for extra storage and a workbench. The home is nestled on a .45-acre lot that has a large, cleared back yard. The upgrades include Double Paned Tilt-In Windows and new Plumbing and Showers in the Bathrooms. In 2022 the entire kitchen was upgraded with new Countertops and Appliances. Crisfield is a small town with big time entertainment. Many public events that draw large crowds are the Crab Derby during the Labor Day Weekend, the Soft Shell Crab Celebration, the Bluegrass Music Festival, Wheels on the Waterfront Classic Car Show, and the J. Millard Tawes Crab and Clam Bake. Crisfield's Waterfront offers Spectacular Views and numerous Public Boat Ramps. Somers Cove Marina is home to Yachts, Sailboats and Seafood Working Boats. Come and enjoy the best that the Eastern Shore offers!

225 N N Somerset Ave, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact:

20949 Somers Rd, Ewell
$315,000
4 Beds ⋅ 3 Baths
Spectacular water views! Welcome to your very own slice of paradise on Smith Island, Maryland! This rare offering is a water and nature enthusiast’s delight. Currently as one of the island's most desirable rentals, this fine property is an ideal weekend/vacation retreat or full-time island home for the most discerning buyer. Existing bookings are already secured for the upcoming season! Enjoy convenient one floor living, situated on almost a full acre of land, including a 20x20 outdoor storage shed. This four-bedroom, two-and almost a-half-bath, cozy and inviting home has many outstanding features. The kitchen, family room, and large sun/recreation room all offer ample space for entertaining. From the new front porch accentuated with a comfortable low country bed/swing overflowing with cozy pillows, to the back deck abounding with scenic views of the marshes and a variety of waterfowl and migratory birds. Upon entering the home, you’ll be greeted with a lovely built-in, electric wall mounted fireplace encased in custom shiplap. It adds ambiance and supplementary heat to the family room. Also, a beautiful bow/picture window overlooks the front yard. The floors are newly installed luxury vinyl plank in the family room, kitchen, bathrooms and hallways. The fully updated kitchen, located just off the family room, boasts a recently installed custom, decorative glass backsplash, new butcher block countertops, and all-new black stainless GE appliances. Through the kitchen, you’ll enter a mudroom space to hang outerwear, coats and jackets. The separate laundry room, which includes a new hot water heater, washer, a new Whirlpool dryer an additional toilet. A beautiful sunroom spans the back of the kitchen featuring built in desk space, large windows and sliding doors. Currently used as a recreation/game room, this three-season room offers spectacular views of the island’s surroundings, including marshes and canals and also has a newly installed mini split for extra cooling and added comfort. The home has four bedrooms, with an additional storage room that could be converted into another bedroom. The primary bedroom is situated on the opposite side of the home from the three bedrooms, providing privacy. It has a newly installed mini split, two large closets, an en suite bathroom with a double vanity, new toilet, and a garden tub with a separate stall shower. The three bedrooms are located on the opposite side of the home and feature a full bathroom, with tub/shower, a linen closet, extra water heater, and access to the attic space. Step outside and you’ll be greeted by a brand-new deck that spans across the back of the house. The sunrise views from this deck are absolutely breathtaking! This home has everything you need: seller offering a one-year home warranty and most of the furnishings will convey. There is also dock space available for your pleasure boat. Most homes on the island need extensive work, but this one is move in ready! If you had to describe this property with just one word, it would be STUNNING! Call today for an exclusive showing.

20949 Somers Rd, Ewell

Listing courtesy of Wilson Realty. Contact:

409 Myrtle St, Crisfield
$154,900
2 Beds ⋅ 2 Baths
Welcome to 409 Myrtle Street, nestled in the heart of Crisfield…proudly known as the Seafood Capital of the World! 🌊🦀 This charming 2-bedroom, 1.5-bath bungalow captures the essence of Chesapeake Bay heritage and small-town coastal charm. Inside, you’ll find a practical and inviting layout featuring a combined living and dining area, a full bathroom, and a half bath currently serving as a laundry room which offers both comfort and versatility. Whether you’re seeking a cozy full-time residence or an ideal seasonal getaway, this home is full of potential and ready for its next chapter. Don’t miss your chance to own a slice of Crisfield’s rich history. Schedule your showing today!

409 Myrtle St, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact: